At first glance, I like your proposal.

One thing that will surprise people is that it contains no provision for numeric comparison, so by the numeric/string duality, numbers will be compared as strings.

I have my doubts about the cases you're not sure about; distinguishing barewords from strings is impossible in non-strict mode (which I rarely use, but which is still a big part of perl, whether you like it or not).

Ranges become flipflops in scalar context and a list in list context, so doing a range comparison seems pretty much inconsistent with the rest of the language.

Comparing lists with any-semantics requires the right-hand side of the ~~ to be evaluated in list context, which IMHO would be a bit surprising.